When I started online, I decided to create my own blogging platform. I am an ASP.Net developer and thought it would be cool to have something other than WordPress, so I'd be able to customize to my hearts content. Big Mistake. Of course the money is in the content, not in spending all your time fixing code, adding features and tweaking stuff that doesn't matter much. 2 years later I have a decent site in a financial niche but the maintenance is preventing me from getting the most from it. My dream would be to convert it to WordPress. I think pumping all the data out of my database and into a WordPress db is do-able, but what really concerns me is to not break any of the URLs. The site is PR5 and has tons of incoming links and search engine traffic. Is it possible to create an .htaccess file or use another method to maintain the existing URL interfaces and seemlessly run a WordPress site beneath it? If it's possible, is it a worthwhile thing to try? [ie: is it risky?] Thanks for your help.
One thing you could do to make sure you don't loose your existing links is to make a list of all of the permanent links you currently have (one for each post I assume), and after you convert your database to wordpress, add in entries doing a redirect from your old link for the post to the new link. An easier way, depending on how you made your own links, would be to just modify wordpress to use permalinks exactly the same as your system did.
Thanks for the tips. Excellent idea! It would really be funny to technical folks who came by and saw a wordpress site where all the pages had a .aspx extension